Sodium borohydride → 6-Methoxy-1-thiophen-2-yl-1,2,3,4-tetrahydroisoquinoline

HRID 397051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397051
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=[N:10][CH2:9][CH2:8]2>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[NH:10][CH2:9][CH2:8]2

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 108002866-Methoxy-1-thiophen-2-yl-3,4-dihydroisoquinoline

Produkt 1

HCID 51632326-Methoxy-1-thiophen-2-yl-1,2,3,4-tetrahydroisoquinolineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (0.916 g, 24.2 mmol) was added in small portions to a solution of 6-methoxy-1-thiophen-2-yl-3,4-dihydroisoquinoline (1.470 g, 6.04 mmol) in MeOH (50 ml) at 0° C. The reaction mixture was stirred for 30 min, warmed to rt and stirred at rt for 21 hr, then quenched by the dropwise addition of H2O (10 ml). Excess MeOH was removed by evaporation and the resulting aqueous solution was extracted with CHCl3 (4×10 ml). The combined extracts were dried over MgSO4 and concentrated in vacuo to give 1.316 g (89% yield) of yellow solid.

Aufarbeitung

  1. stirringstirred at rt for 21 hr
  2. customquenched by the dropwise addition of H2O (10 ml)
  3. customExcess MeOH was removed by evaporation
  4. extractionthe resulting aqueous solution was extracted with CHCl3 (4×10 ml)
  5. dry with materialThe combined extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-512fec893adc4ee89ba59f9e1add20a5
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608203B2

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